Sissy Secretary Stories

20,580 results
Orientation
Length
Source
Infinite Scroll

Sexual Sixpack

by SciGuy on Sep 16, 2017
Transsexuals & Crossdressers

The average person, applying contemporary community standards, would find that this work, taken as a whole, appeals to prurient interest only, and is utterly without redeeming social value. And that's what makes it fun. ***** 1.Realization So. Last night you got gang banged. Damn! It was your choice, no one slipped you any drugs, you weren't drunk. Well,...

The Set Up

by undermythumb10 on Sep 15, 2017
Fetish

Difficult to know where to start, I'm sat tied to a chair with a pair of my step daughter panties position on my head so the crutch is placed over my nose, I've been sat like this for four hours thinking about how my life has changed over the past 3 months. I was once a successful business man running a medium size company with 50 employees, single and very...

Sissy's Decline into a Slut Pt. 05

by Sissy_Chantel on Sep 16, 2017
Transsexuals & Crossdressers

Chapter Seven: I've been taken, Made into a Maid, Turned out as a Slut. Two days have passed by, it's Thursday morning. Today Master Gage and Master Martin are to arrive by 10:00am. I awake by 8:00am and my stomach is turning. I get up sit on the edge of my bed wearing my sleeping lingerie today it's a white satin full slip, white lace bra and satiny panty....

Mistress X 02: Pixie's Predicament

by Long2bLocked on Jan 22, 2019
BDSM

Note to readers: This short story is not part of any series. The setting and characters are based on those from my "Laura's Femdom" stories. My Mistress X stories stand on their own but are best read in order. This particular story describes a predicament bondage session. ***** Mistress Alexis X has a female live in slave named Pixie. She works at Red Ro...

Carol's Gifts

by Belongs2Beth on Sep 16, 2017
BDSM

Authors note: This is the third story featuring characters introduced in "Carol's Christmas." In this installment Carol give's Jack his Christmas gift one night late with the help of Irena, "Marcia" and several well hung younger men. The sex action in this story is unrestrained, and since the tags are at the bottom of the page, I will issue the following mil...

Transforming Brent Pt. 03

by sissymissyct on Oct 8, 2019
Fetish

Over the next few days I removed most of my male clothing from the house and donated it to Goodwill. I met Wendy as she got out of work each day and we went shopping. The first time was for regular clothing. Skirts, dresses and blouses, leggings and shoes and regular lady's sportswear. Thursday it was lingerie night. I ended up with multiple bras and camiso...

Mike the Gang Bang Bitch

by sissyneko on Mar 17, 2020
Transgender & Crossdressers

Standing in the bathroom wearing just his little pink bikini panties and stockings, Mikes gaze was transfixed. Not on the panties, the usual draw of his lust, or even his white thigh high stockings with their little pink bows at the top. None of that drew his attention, it was the bathroom itself, it was run down, dingy and in the worse part of town. But non...

Twist

by Seurat on Sep 12, 2017
BDSM

Once, long ago, I got fed up with the way femdom, forced transgender, and loving wife stories with BDSM basis ended; they had grown very predictable. In fact, a few authors had posted short lists of vignettes which, unintentionally, encompassed all of the common endings which I had grown to abhor. My own list, a response to the predictability of those storie...

Dear, We Have to Talk Ch. 07

by dr13bone on Sep 25, 2017
Interracial Love

"You can look at them, but don't touch!" my wife said in a teasing tone as she got dressed for work. She made a point of lifting her tits up, the thick gold rings through the nipples shined in the light from the lamp in the bedroom. It was Mindy's first day back at her old office. I handed over to her the white lacy bra she wanted to wear. It was new, all h...

Heidi’s Submission

by TimT1972 on Sep 19, 2017
Transsexuals & Crossdressers

Eighteen year olds are the same the world over. The handsome, tough and sporty are nearly always the most popular. Adam was none of these, he was rather effeminate, of slight build and definitely no sportsman. As such, he never had that many friends. His home life wasn't much better; his father was dead, he had no siblings and his mother worked every hour Go...